N-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxan-3-yl]acetamide

• ChemBase ID: 174477
• Molecular Formular: C18H21NO8
• Molecular Mass: 379.36124
• Monoisotopic Mass: 379.12671664
• SMILES: [C@H]1([C@@H]([C@@H]([C@H](O[C@H]1CO)Oc1ccc2c(c1)oc(=O)cc2C)NC(=O)C)O)O
• Canonical SMILES: OC[C@@H]1O[C@H](Oc2ccc3c(c2)oc(=O)cc3C)[C@H]([C@H]([C@H]1O)O)NC(=O)C
• InChI: InChI=1S/C18H21NO8/c1-8-5-14(22)26-12-6-10(3-4-11(8)12)25-18-15(19-9(2)21)17(24)16(23)13(7-20)27-18/h3-6,13,15-18,20,23-24H,7H2,1-2H3,(H,19,21)/t13-,15-,16+,17-,18+/m1/s1
• InChIKey: QCTHLCFVVACBSA-LHKMKVQPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(4-methyl-2-oxochromen-7-yl)oxy]oxan-3-yl]acetamide
• Synonyms: 7-[[2-(Acetylamino)-2-deoxy-α-D-galactopyranosyl]oxy]-4-methyl-2H-1-benzopyran-2-one; GalNAc1-α-4MU; 4-Methylumbelliferyl 2-Acetamido-2-deoxy-α-D-galactopyranoside

Database IDs

• CAS Number: 124223-99-0
• PubChem SID: 164230387
• PubChem CID: 14345477

CALCULATED PROPERTIES

• Acid pKa: 11.977438
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -0.7769147
• LogD (pH = 7.4): -0.7769247
• Log P: -0.7769144
• Molar Refractivity: 91.0572 cm^3
• Polarizability: 36.148544 Å^3
• Polar Surface Area: 134.55 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Warm Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 257-260°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M333500

An effective substrate for the detection of N-acetyl-α-D-Galactopyranosiaminidase activity. The deficiency of this enzyme is the defect in Schindler disease.

REFERENCES

• Szweda, R., et al.: Can. J. Chem.. 67, 1388-1391 (1989)
• Puri, K.D., et al.: J. Biol. Chem., 268, 16378 (1989)